methyl 4-O-benzoyl-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside | 1214746-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside
• 英文别名: TBDMS(-2)[TBDMS(-3)][Bz(-4)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 1214746-48-1
• 化学式: C₂₆H₄₆O₇Si₂
• 分子量: 526.818
• InChiKey: CSHZOOHMCLDTTB-AREVGRJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (((2R,4αR,6S,7R,8S,8αR)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl)bis(oxy))bis(tert-butyldimethylsilane) 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以95%的产率得到methyl 4-O-benzoyl-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Regioselective Control in the Oxidative Cleavage of 4,6-O-Benzylidene Acetals of Glycopyranosides by Dimethyldioxirane

  摘要：

  The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates lent yields. With a Proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.

  DOI：

  10.1021/jo9026098

文献信息

• Regioselective Oxidative Cleavage of Benzylidene Acetals of Glycopyranosides with Periodic Acid Catalyzed by Tetrabutylammonium Bromide
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-0033-1340056

  日期：——

  A combination of periodic acid, tetrabutylammonium bromide, and wet alumina in dichloromethane efficiently oxidized benzylidene acetals of carbohydrates to the corresponding hydroxybenzoates in excellent yields (>90%). Under these conditions, other protecting groups, such as tert-butyl(dimethyl)silyl, tert-butyl(diphenyl)silyl, and functional groups, such as epoxide, were unaffected. By varying the

  高碘酸、溴化四丁基铵和湿氧化铝在二氯甲烷中的组合有效地将碳水化合物的亚苄基缩醛氧化为相应的羟基苯甲酸酯，产率极好 (>90%)。在这些条件下，其他保护基团（例如叔丁基（二甲基）甲硅烷基、叔丁基（二苯基）甲硅烷基）和官能团（例如环氧化物）不受影响。通过改变 C3 位置保护基团的性质，获得了对 4-或 6-苯甲酸酯的良好到高的区域选择性。
• Regioselective Control in the Oxidative Cleavage of 4,6-<i>O</i>-Benzylidene Acetals of Glycopyranosides by Dimethyldioxirane
  作者：Arnaud Stévenin、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1021/jo9026098

  日期：2010.3.5

  The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates lent yields. With a Proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.